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Who Are You Dressing For, Really?

"Style, like love, is fluid and shifts with the seasons of our lives."
Black and white photo of a woman holding a leopard print Prada bag

In the autumn of 2024, the first thing on my post-break-up agenda was an overhaul of my surroundings. I didn’t cut off all my hair, I didn’t book an extravagant trip and I certainly did not seek comfort in a rebound — but I did go buck wild with decluttering. Not to negate any of the aforementioned coping mechanisms, but breaking up can be expensive enough, and what better way to reclaim a sense of agency over one’s life than to clean out an overflowing wardrobe?

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In my last relationship, roughly 30 per cent of my clothes saw the outside of my apartment. Not because my then-partner had any say in what I wore, but because, as humans, love influences our choices. You find yourself unconsciously reaching for the things you know your SO likes on you and, in turn, avoiding what they don’t. Even my worst ex never explicitly requested anything about my clothes.

“In the ebb and flow of domesticity and cohabitation, something was lost.”

But, after a while, I noticed I’d stopped wearing bolder lipsticks due to complaints about making out, my footwear leaned towards sensible varieties because he loved a post-dinner stroll and my obsession with pinning vintage brooches to my coat had quietly withered because they reminded him of his grandma — not very hot. I’d become practical. Still me, but a reconfigured version that brought forward the parts of me that connected me to him. 

In the ebb and flow of domesticity and cohabitation — meal prepping, chore divvying and shared Google Calendars — something was lost, slowly convincing me that dressing up should be saved for occasions, of which there were less and less. Fast-forward to a newfound singledom, and the weeks-long process of cleaning out my closet revealed these buried parts. I stumbled upon forgotten pieces, like a pleated Chanel skirt from the ’90s that could have given ‘nanna’ to the uninitiated, or the limited-edition Issey Miyake that an ex described as “brazen”. I greeted them like old friends and wondered why I let so much time go by between catch-ups.

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Relationships can tether us to something beyond ourselves, providing these railings in life that dissipate when we part ways. More often than not, it’s these guides we mourn. We grieve the promise of simplicity and partnership in choices and whatever life throws at us — a security that sometimes manifests in what we wear. When you lose the sounding board of someone else’s gaze, it can provoke a strange recalibration. You start noticing all the things that you had quietly stopped wearing, not because anyone forbade them, but because they didn’t fit into the rhythm of the relationship. And in losing that sense of control and certainty in one area, perhaps we’re inspired to find it elsewhere.

“I was left with just me, my clothes and the deafening silence that followed the comically dramatic question: who am I dressing for now?”

As I stood before my empty wardrobe and a pile of boxes bound for the thrift store, I was left with just me, my clothes and the deafening silence that followed the comically dramatic question: who am I dressing for now? Suddenly, the possibilities opened up. Life was more than grocery runs and the odd date night at the local pub. That’s not to say I resented any part of that, but it didn’t present many opportunities for dressing up. Now, though, there were other stakes at play. As a single person, I leaned into experimentation. Every day, an outing presented infinite possibilities, and there was no-one to roll their eyes at my brazen outfits. 

But when taking on the uniquely painful challenge of dating in the digital age, a new limitation emerged. The city can feel obscenely small at times, and the chances of running into someone you’d rather not see become alarmingly high when you’re also part of the floating purgatory of dating apps. Wherever you go, it can introduce an element of anxiety over how you look when out and about — ripe to be perceived by thousands of other judgemental singles at any moment. Suddenly, I became acutely aware of the more stressful part of IRL meet-cutes. 

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For others, being in a healthy relationship can provide the kind of security and self-confidence boost that make them feel emboldened to show off a little more. As Esther*, 30, tells me, she feels empowered to dress most like herself when she feels secure in her relationship. “Maybe something in the back of my mind tells me that nothing’s going to repel him at this point, so I might as well get a little funky with it,” she says. “When I was single, I felt the need to be more consistent with my style — palatable, as if I could be spotted by a date’s mother and get her pre-approval.”

Sure, I like to think I have an unflinching sense of personal taste. Yet, in the dressing room, it’s not just my voice that echoes. There is the subtle nag of my mother to accentuate my figure more, the smile of my partner when I wear the colour I wore on our first date and even the scrunchie I have convinced myself is good luck because a friend mentioned she knows it’s going to be a good time when I wear it. A passing compliment here, a lingering stare there — it all gets sewn into the seams of who we are and who we want to be.

“Style, like love, is fluid and shifts with the seasons of our lives.”

Even now, as I navigate the waters of new love once again, the familiar sense of another ‘me’ taking shape materialises. Will this top become one we joke about? Will this dress be worn on our first trip together? Which outfit will be quietly retired because it doesn’t quite fit into the version of life I’m creating with them? With these familiar uncertainties — wondering which parts will inevitably become part of the fabric of our story, which ones might find new life breathed into them and what will inevitably be left behind — comes a subtle sense of guilt, too. Did the women before me really protest to wear whatever they want just for me to adapt to a relationship? But what I’ve come to realise is that dressing isn’t about erasing yourself or becoming someone new for someone else; it’s about curating the collage that makes sense for you. Adding layers, shedding some. Embracing the fingerprints of the people we love and have loved, and the impression they have left on the way we show up in the world — without ever erasing our own, of course.

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Style, like love, is fluid and shifts with the seasons of our lives. It means sometimes wearing my hair in a ponytail because it makes my mum happy when she can “see my face”, and, when struggling to decide, leaning towards the blue pair of swimmers my friend says reminds her of our backpacking days. Maybe style is like love in the way that we don’t choose one version of ourselves and stick to it forever, but we try things on, seeing what fits and allowing ourselves to be moved by those who see us, even when we don’t see ourselves. 

Just as my face is made up of the people who came before me — my father’s eyes, my mother’s cheekbones — my tastes and desires aren’t wholly my own either. And while that once filled me with confusion, it’s something I’ve come to take great comfort in. In a time when personal style seems to evoke such existential dread, removing myself from the equation feels profoundly liberating.

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